In 20th century linguistic philosophy there was a popular idea developed to explain a lot of misunderstandings people can make in language. Language can be regarded numerous ways in formal logic, such as with propositions or predicates and even just with representative symbols. In that context it’s easy to see categorical errors used in language.
Usually people aren’t aware of making categorical errors. Your question is complex combing ideas about time and mathematically about probabilities. Categories that are juxtaposed included the relation of probabilities to physical systems I suppose and if those probabilities are predetermined or not…
“Does time make improbability more probable?”- it’s a good question to write about yet possibly too complex to answer outside of a specific context. Consider the challenges of accurate weather predictions in relation to time.
Garrison Gibson: books and blog 